7 Go-to-Market Lessons from Rising Team’s Path to Fortune 500 Customers

When you incorporate a company in April 2020, you’re either spectacularly unlucky or accidentally brilliant. For Rising Team CEO Jennifer Dulski, it turned out to be the latter. But timing alone doesn’t build a customer base that includes Google, Cisco, and Airbnb. That requires getting specific go-to-market decisions right—and learning from the ones you get wrong.

In a recent episode of Category Visionaries, Jennifer shared the tactical lessons from building a team performance platform that now serves Fortune 500 companies, school teachers, and even Massachusetts probation officers. These aren’t theoretical frameworks. They’re the hard-won insights that separate growing startups from stalled ones.

Lesson 1: Product Pivot Based on Time Efficiency, Not Just Effectiveness

Rising Team’s original product focused on one-on-one manager sessions with team members. The logic was sound: personalized attention leads to better outcomes. But logic doesn’t always win in the market.

“The very first version of the product was built mainly for managers to use one on one with each person on their team,” Jennifer explains. “And then what we realized and what was the huge unlock for the growth of the company was that doing this as a team would be more effective for two reasons. One is it saves a lot of time, you know, it’s much faster to get the whole team together in one meeting than to meet each person separately.”

The insight that changed everything wasn’t about effectiveness alone—it was about efficiency combined with a deeper human need. Teams don’t just benefit from connection; they actively crave it. This realization transformed both the product and the sales motion. Instead of selling time-intensive individual sessions, Rising Team could demonstrate immediate time savings while delivering stronger outcomes.

For founders building in the team collaboration or performance space: your buyers aren’t just optimizing for results. They’re optimizing for results per hour invested. If your solution requires significant time commitment without proportional return, you’re fighting an uphill battle regardless of efficacy.

Lesson 2: Unlimited Pilots Sound Good but Kill Activation

Here’s a counterintuitive truth about pricing pilots: constraints drive action. Jennifer learned this through experience that cost months of momentum.

“When I first started, I was like, we just need to get people to use this, whatever it takes. And I offered unlimited teams for $1,500 for some short period of time, and a lot of people bought it, but then they didn’t really use it,” she recalls. “There wasn’t really an incentive to get going with unlimited teams and so forth.”

The solution wasn’t to make pilots cheaper or shorter. Rising Team went the opposite direction: twelve-month pilots with several hundred people, sized appropriately for statistical significance. The reasoning? Enterprise expansion decisions require data, not anecdotes.

“Initial pilots need to have enough people in them and be run over a long enough time period that we can gather data to really clearly prove ROI,” Jennifer notes. “That’s what gives you statistically significant data to prove that it’s working. And that’s what then gives people the reason to see the ROI and continue expanding.”

This is the pilot pricing paradox: making it too easy to say yes often means making it too easy to ignore. The companies that signed up for unlimited short-term pilots lacked the incentive to implement quickly and broadly. The companies that committed to structured twelve-month pilots had skin in the game and champions who needed to show results.

Lesson 3: Enter Through Jobs to Be Done, Not Category Definitions

Rising Team sits at the intersection of learning and development, team engagement, and team building. That’s usually a positioning nightmare. But Jennifer turned it into an advantage by focusing on entry points rather than category ownership.

“We call it a team performance platform. I believe that is in some ways a new category,” she explains. “The categories that we tend to compete against are either learning and development. So learning management systems, facilitators, they hire to do trainings or team engagement, measurement and movement, and then possibly a third category, which is kind of just pure team building.”

But here’s the tactical shift: Rising Team doesn’t force buyers to understand or accept a new category upfront. They capture demand from specific, acute pain points:

• Pulse scores came back bad and need immediate improvement
• Offsite budget was eliminated but team still needs connection
• Distributed team feels disconnected and engagement is dropping

“We often come in through one of the, if you will, jobs to be done of things like my pulse scores came back and they’re really bad. I need help moving them or I no longer have an off site budget. How do I still keep my team connected?” Jennifer notes.

The category positioning becomes relevant after the initial sale, when explaining why Rising Team delivers better outcomes than traditional alternatives. This sequencing—solve problem first, educate on category second—removes friction from the buying process while still building toward category creation.

Lesson 4: The First Logo Matters Less Than the First Data Set

Most founders obsess over landing that first major logo. Rising Team’s first enterprise customer was Bank of Hawaii—not exactly the obvious early adopter for a Silicon Valley startup. But that’s precisely what made it valuable.

“We got an introduction to them and, you know, sometimes it just takes a like a passionate early adopter and you wouldn’t think necessarily of a bank as being an early adopter, but in this case they had a CEO who said, yeah, I really see the potential here,” Jennifer recalls.

The real value wasn’t the logo. It was what Bank of Hawaii enabled: a proper data set. They started with a pilot, rolled out to more of their organization, and within six months decided to deploy company-wide. Now, years later, the data is definitive.

“You can see based on the number of Rising Team sessions people run, their engagement scores go higher, their manager effectiveness scores go higher. We just got data back that shows we drive a significant lift in employee retention for them,” Jennifer explains.

This data set becomes the foundation for every subsequent enterprise sale. When a CIO asks for proof, Rising Team doesn’t rely on case studies or testimonials. They show statistically significant improvements in metrics that CFOs care about. Your first customer should be chosen not for brand recognition but for their willingness to generate the data you’ll need to close customers two through twenty.

Lesson 5: Build a GTM Team Structure Around Velocity, Not Specialization

Rising Team runs their entire go-to-market motion with five or six people total. One person dedicated to marketing. No massive content team, no field marketing organization, no separate SDR function.

“At a startup, our number one value at Rising Team is we’re all one team. And so the idea is when things need to be done, people are going to raise their hand and they’re going to jump in and do it,” Jennifer notes. “And that means everybody does both their job and things that may be slightly outside the scope of their job.”

This isn’t about being scrappy or wearing multiple hats out of necessity. It’s a deliberate structural choice that enables rapid experimentation. When you have five people instead of fifty, you can test a new landing page approach in days instead of weeks. You can kill underperforming experiments without political fallout.

The team runs rigorous growth experimentation—hypotheses, quick tests, measurement, iteration. Recent example: they added more fields to their demo signup form to better route leads by company size. Conventional wisdom says more fields kill conversion. Their data showed the opposite: conversion rates actually increased.

Meanwhile, their homepage chatbot—the thing everyone said they needed—hasn’t meaningfully moved the needle yet. The lesson isn’t about specific tactics. It’s about building a team structure that can discover what works for your specific context through rapid iteration rather than following best practices.

Lesson 6: Sell to Functional Leaders with Budget and Pain, Not Titles

Rising Team doesn’t target “enterprises” or “HR buyers.” They target functional and divisional leaders at large companies who control budgets and experience acute pain.

“We tend to sell to functional and divisional leaders at large companies who have these pain points,” Jennifer explains. “Sometimes it’ll be a CMO or a CIO or a VP of engineering who says, I really want something like this for my team.”

These buyers have three critical characteristics:

First, they control actual budget—not unlimited budget, but enough to run a meaningful pilot without requiring approval from six layers of management.

Second, they personally feel the pain. Their team is disconnected, their engagement scores are declining, or they just had their offsite budget cut. They’re not evaluating solutions academically; they’re looking for something that solves a problem they’re accountable for solving.

Third, they have the authority to expand. When the pilot succeeds, they can scale within their division and become internal champions who open doors to other parts of the organization.

“As an example, we have a big tech company, we have their cloud. And then just yesterday, someone from their cloud moved to a different part of the organization, says, now I want to use this over here,” Jennifer notes.

This land-and-expand motion happens organically when you sell to the right initial buyers. They become your internal sales force because the results speak for themselves and they carry the product to their next role.

Lesson 7: Optimize Investor Selection for Alignment, Not Valuation

Jennifer raised Rising Team’s entire funding on Zoom. She met only one investor in person before closing the round. Several investors she still hasn’t met face-to-face. This isn’t a pandemic adaptation—it’s what fundraising looks like when you optimize for the right variables.

“It’s not necessarily true that the people who give you the absolute highest valuation and the absolute most money will be the best investors over the long term,” she explains. This comes from someone who teaches scaling companies at Stanford’s business school, where she regularly sees case studies of founders who made this exact mistake.

“I’ve seen this really well because I teach in class where I bring in guests and we do cases of other peoples businesses and there are so many examples of people kind of choosing the wrong investors. So I feel like we’ve chosen our investors very thoughtfully and we have an incredible group of investors who feels really mission aligned, really focused on the long term, really supportive of the company.”

Mission alignment and long-term orientation beat valuation optimization every time. The extra points on valuation might feel good for a week. The wrong investor will make every subsequent decision harder for years. Choose investors the way you choose co-founders: for the multi-year journey, not the signing bonus.

The Through-Line

These seven lessons share a common theme: they’re all about making decisions that optimize for the right outcomes rather than following conventional playbooks. Longer pilots instead of shorter ones. Smaller teams instead of specialized functions. Lower valuations from better investors instead of higher valuations from whoever offers them.

Jennifer’s vision for Rising Team is ambitious: “I believe that we can help every team on earth be more successful, more connected, and more engaged.” That vision is backed by data showing improved engagement scores, manager effectiveness, and employee retention. It’s being validated by customers ranging from Fortune 500 tech companies to school teachers to Massachusetts probation officers.

But the tactical lessons from getting there? Those are universally applicable to any B2B founder trying to figure out what actually works versus what’s supposed to work according to the playbook everyone else follows.